Ultimate Thailand Itinerary – First Time Thailand With Affordable Luxury Accommodations

Thailand Itinerary

Thailand is one of the top destinations for tourism and undoubtedly one of the best places for affordable luxury. Popular amongst luxury travelers and backpackers alike, for a country so swarmed with tourism, Thailand has still been able to maintain much of its cultural charm. Factor in that it is one of the most affordable countries to travel to, and you’ve found yourself one of the best places to experience an ultimate Thailand itinerary while staying in luxury accommodations without the high price tag. A country so rich in culture and natural beauty, paired with warm weather year-round, it is no wonder why many expats choose to make Thailand their home. My flexible 10 day – 2 week thailand itinerary will show you the most popular cities and islands for the ultimate first-time trip to the country who’s nicknamed “The Land of Smiles.”

Low Season Thailand

Thailand generally has two seasons: low season and high season. During low season (May through October) heavy rains do occur, and there are rare chances of monsoons. However, the rain fall is usually not continuous and often clears up to beautiful sunshine. During the rainy season, 5 star accommodations can cost under $100.00 USD a night. Even better, with the average massage costing around $15.00 USD, you can’t afford NOT to get one every day; especially when the average meal price can be as little as a couple dollars for some of the best Thai food you’ll ever have the pleasure of tasting. High season is when all the prices increase to double, triple, or even quadruple the cost. The peak season of Thailand occurs from January – March. If you choose to visit Thailand during this time, be sure to book accommodations at least 3 months in advance to help with costs. The most optimal times to visit Thailand would be just before high high season or just after.
 Chiang Mai

The Most Ideal Thailand Itinerary

3-5 nights in Chiang Mai

Begin your trip in the northern city of Chiang Mai to enjoy a fully immersive cultural experience. Explore authentic Thailand at its best from the city to the jungle, and from temples to night markets. Some must-dos of Chiang Mai include:
  • Take a half day cooking class to learn how to make (and get to eat) all your favorite Thai dishes. This will easily be one of the best and your most favorite meal had in Thailand. Come hungry!

    may kaidees
    Vegan Cooking Class
  • Volunteer a day or half day at Elephant Nature Park – one of the few true and ethical elephant sanctuaries in Thailand, where elephant riding is NOT allowed. At ENP you will get to feed, bathe, and play with these amazing gentle giants all while learning about the awful elephant tourism industry of Southeast Asia, and how ENP helps to rehabilitate the elephants after years of mistreatment and abuse. (Please never ride elephants!)

    Top things to do in Chiang Mai
    Elephant Nature Park
  •  Take a couple of hours and visit the sacred sites and temples, such as Chiang Mai’s most famous temple, Wat Phra That Doi Suthep. Another popular temple, Wat Suan Dok even allows you to sit and chat with a monk to help them practice their English!

    Wat Phra That Doi Suthep Chiang Mai
    Wat Phra That Doi Suthep
  • Plan a day or over-night trip to a neighboring northern city such as Pai or Chiang Rai to explore more of northern Thailand’s culture and natural beauty.
  • Jump on a half-day tour of either trekking through the jungle, or zip-lining through the jungle (the longest zip-line in Asia) at Flight of the Gibbon,
  • Receive as many massages as your body can handle. Don’t bother with fancy hotel spa massages that charge western spa prices. There are so many incredible spas in Thailand where a traditional Thai massage will cost anywhere from 200 – 700 BAHT.  One of the most popular spots to get a cheap massage in Chiang Mai is surprisingly at the Women’s Correctional Institution, where you can get massaged by a prisoner. For something a little more conventional, my favorite massage in Chiang Mai was at Makkha Spa, where each treatment is accompanied by a cup of tea and the most delicious mango sticky rice.
  • Shop, eat street food, and wander the night bazaar, and especially do not miss the Sunday Night Market – the biggest night market in all of Asia. Be sure to get there as early as they open (around 5:00PM) as crowds will heavily build later in the evening making it more difficult to navigate.

Best Place to Stay in Chiang Mai

Recommended accommodations from ultra luxe to affordable luxe – Four Seasons, Shangri-La, Anatara, Le Meridien, or if you prefer Airbnb, the Astra Condos are nice and modern with a rooftop infinity pool that has spectacular views. (Condos at the Astra can be found on Airbnb, expedia.com, hotels.com, and booking.com.) I’ve also heard great things about the condos offered through Stay in Chiang Mai. Lastly, there are also no shortages of boutique hotels in Chiang Mai that offer nice accommodations for every budget.

Best Time to Visit Chiang Mai

Weather-wise, Chiang Mai is best visited during November-February. Because Chiang Mai is in the north, it is a bit colder compared to the cities and islands in the South of Thailand. Even in the summer, it can get especially chilly at night. Chiang Mai is especially exciting during the major festivals, such as the exciting Loi Krathong festivities of November, and the beautiful Chiang Mai flower festival in February.

 Koh Samui Beach

3 – 4 nights Koh Samui  

Next, continue your Thailand itinerary by making your way down south to the island of Koh Samui. Situated on the gulf side of Thailand, this larger-sized island has a lot to see. Some highlights for Koh Samui include:
  • Relaxing on one of the many white sand and clear blue water beaches such as Koh Samui’s longest beach, Mae Nam.
  • Party and enjoy the bustling nightlife in the beach of Chaweng.
  • Receive an ocean view massage at Cyan spa, then walk the streets of Bophut AKA the Fisherman’s Village, and enjoy sunset on one of the many beachside bars and restaurants.
  • Visit the famous site of Samui Big Buddha.

    Big Buddha Samui
    Big Buddha of Koh Samui
  • Take a day or overnight trip to a nearby smaller island of your choice, such as Ko Pha-ngan (famous for their wild full moon parties) or Ang Thong National Marine Park.

Best Place to Stay in Koh Samui

Recommended luxury accommodations from ultra luxe to affordable luxe: Four Seasons, Banyan Tree, Le Meridien, Sheraton Samui Resort

Best Time to Visit Koh Samui

Koh Samui has the best weather from about February to October. Koh Samui is an island, so if sunny and dry beach weather is on your radar, the best months to visit would be February and March. You still may get lucky during low season months, and find plenty of sunshine while you enjoy the beaches.


Phuket Luxury

3 -5 nights in Phuket/Krabi/Koh Phi Phi  

Finally, jump to the Admanean sea side island of the Phuket/Krabi region. Spend a few nights in Phuket for the bustling, quintessential touristy Thailand experience, where a mix of beaches, city life, and cultural sites will make you experience all Thailand has to offer at once. For a more luxurious experience, stay in a private pool villa at a resort such as The Westin in the serene and tranquil Siray Bay, away from main Phuket Town; or any of these hotels depending on your budget. Phuket has the most options for luxury accommodations at every price point, so it won’t be difficult to find something that is perfect for you. Some highlights of Phuket include:
  • Have an insane nightlife experience on Bangla Street in Patong Beach, complete with infamous Ping Pong shows and ladyboy dancers.
  • Witness excellent views of Phuket from the Big Buddha statue.

    big buddha
    Phuket Big Buddha
  • Spend a night or two in Railay Beach in Krabi for unforgettable pristine beaches.
  • From either Phuket or Krabi, take a day or overnight trip and tour the Phi Phi islands, where you can snorkel/dive, and visit other famous islands such as the stunning Maya Bay (where the movie the Beach was filmed), kayak through the caves of James Bond Island, and witness the wild monkeys of Monkey Beach.

Best Place to Stay in Phuket

Recommended luxury accommodations from ultra luxe to affordable luxe: Trisara Villas & Residences PhuketThe Shore at Katathani, The Westin Siray Bay

Best Time to Visit Phuket

The best weather on Phuket occurs between November and April. If you plan to take day trips to surrounding islands, good weather months should be considered as severe rain can cancel boat trips and impede on plans. If this is a concern for you, monsoon season last from about May through October so those months should be avoided. Still, Phuket is always pretty warm and the rains are tropical so they do have a tendency to clear up and bring on some sunshine.

Koh phi phi
Koh Phi Phi Islands / Maya Bay

FAQ: How to get Around Thailand 

The best way to explore the cities and islands of Thailand is by motorbike/scooter and should cost no more than around 250 BAHT (~$8.00 USD) a day. If a motorbike is not for you, taxis are very cheap but be be sure to negotiate. Negotiate everything in Thailand as  there are many tourist traps. Be especially aware of Tuk Tuk rides, they shouldn’t be more than a couple hundred BAHT and do not allow them to take you anywhere other than your agreed upon destination.

Getting from one city to the next is most efficiently reached by short plane rides and usually costs no more than $100 USD. For a more economical route, an overnight sleeper train is a good option.

The only way to get to the islands is by boat. A speedboat is the quickest but also most expensive. You may take a ferry for a cheaper option but it will take a bit longer to reach your destination.

With a country that has so much to see and do, a couple weeks in Thailand is not nearly enough time to see it all. I can’t wait to come back to explore the more remote and off-the-beaten-path cities of Thailand, and I especially can’t wait to explore some of the more untouched and secluded islands. If you’ve been to Thailand, which city or island is your favorite?

Best Beaches in Thailand

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15 thoughts on “Ultimate Thailand Itinerary – First Time Thailand With Affordable Luxury Accommodations

  1. Really enjoyed your post and your itenary will help me plan for my next visit. The photos just say it all. Thanks for sharing and inspiring.

  2. This is super helpful for trip planning! The vegan cooking class in Chiang Mai is a great idea. I didn’t realize Thai food and veganism went together that well 🙂

    1. It is actually super easy to eat vegan/vegetarian in Thailand! Especially in Chiang Mai – they have tons of vegan cafes and many restaurants offer a vegan menu. Just remember to ask for “no fish sauce” whenever ordering out because they use it in everything!

  3. We’re headed back to Thailand in August and September, so will definitely be bookmarking this to help us with our Koh Samui itinerary. Beautiful photographs, too!

  4. We were in Thailand as a family, and LOVED it! We were so pleasantly surprised by how affordable it really was – you are absolutely right – a Massage is a MUST. We didn’t make it to Chiang Mai, so I keep stalking blogs that talk about it. I so very much want to go back. 😀

  5. I haven’t been to Thailand yet, but it is very high on my bucket list! I love that there are so many affordable, luxury things to do there. The elephant sanctuary sounds fantastic!!

  6. There’s so much things to do in Thailand it can be overwhelming so very nice guide ! It’s nice to know there are so many affordable luxury accommodations around, the country looks so beautiful

  7. I have been to Thailand one time. We went because I got a super deal including flights, hotels, and breakfast for a dirt, cheap price. To date, it has been one of the best travel deals of my life. We stayed on pretty nice hotels and ate delicious food from the street almost every day. So, I totally get the concept you are presenting in here. I want to go back to the country since I have not been to any of the islands. I would love to experience more.

  8. I went to Thailand very very long time ago and I want to explore these places again since at that time places like Koh Samui were not very popular. Thank you for this wonderful itinerary with great insight. You made my life easier and saved me time. Also, the post is written beautifully 😊❤️

  9. Chiang Mai is such a great city and I loved Wat Phra That Doi Suthep. Unfortunately, I didn´t take a cooking class or visit an Elephant Camp. This sounds like a lot of fun! Also Railay and Koh Phi Phi are amazing places no one should miss when visiting Thailand. I travelled through the country during high season so everything was more expensive but it was so amazing anyway.

  10. Lovely! This is very helpful itinerary for Thailand. Planning to visit the country soon and I’m happy to know that you can enjoy luxury accommodation for an affordable price. I’ll take note of this. Thanks! 🙂

  11. Definitely saving this for when I finally make it to Thailand – love the “affordable luxury” focus since that’s pretty much how we prefer to travel;

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